An unprecedent improvement in the reaction rate (from hours to minutes) was observed during the In-mediated allylation of isatins with allyl bromide in the presence of N-Boc-glycine. The observed phenomena was generalized as a general protocol for the allylation of differently substituted isatins with excellent yields in a short time and with a wide range of functional group tolerance. Evidence suggests the unique role of the N-Boc-glycine additive was to increase the rate of formation and increase the nucleophilicity of the allylindium organometallic reagent.
“N-Boc-glycine-assisted indium-mediated allylation reaction: A sustainable approach”
Sandeep Reddy Vemula, Dinesh Kumar, and Gregory R. Cook*
Tetrahedron Lett. 2015, 56, accepted for publication
special edition in honor of Prof. Harry Wasserman